US4526979A - Carbamates and oxalamides of amino-N-(1H-tetrazol-5-yl)benzamides - Google Patents

Carbamates and oxalamides of amino-N-(1H-tetrazol-5-yl)benzamides Download PDF

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Publication number
US4526979A
US4526979A US06/517,085 US51708583A US4526979A US 4526979 A US4526979 A US 4526979A US 51708583 A US51708583 A US 51708583A US 4526979 A US4526979 A US 4526979A
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US
United States
Prior art keywords
tetrazol
phenyl
aminocarbonyl
amino
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US06/517,085
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English (en)
Inventor
Norton P. Peet
Shyam Sunder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aventis Pharmaceuticals Inc
Original Assignee
Merrell Dow Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merrell Dow Pharmaceuticals Inc filed Critical Merrell Dow Pharmaceuticals Inc
Priority to US06/517,085 priority Critical patent/US4526979A/en
Priority to AU30222/84A priority patent/AU561513B2/en
Priority to CA000459075A priority patent/CA1220209A/en
Priority to JP59147033A priority patent/JPS6042371A/ja
Priority to ZA845518A priority patent/ZA845518B/xx
Priority to DE8484108508T priority patent/DE3466537D1/de
Priority to AT84108508T priority patent/ATE30024T1/de
Priority to IL72431A priority patent/IL72431A/xx
Priority to NZ208935A priority patent/NZ208935A/en
Priority to EP84108508A priority patent/EP0135032B1/en
Priority to PT78944A priority patent/PT78944B/pt
Priority to GR75368A priority patent/GR82102B/el
Priority to HU842827A priority patent/HU191431B/hu
Priority to IE1894/84A priority patent/IE57604B1/en
Priority to ES534532A priority patent/ES534532A0/es
Priority to DK358584A priority patent/DK159776C/da
Priority to NO842967A priority patent/NO168641C/no
Priority to KR1019840004338A priority patent/KR890000534B1/ko
Assigned to MERRELL DOW PHARMACEUTICALS INC. reassignment MERRELL DOW PHARMACEUTICALS INC. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: PEET, NORTON P., SUNDER, SHYAM
Application granted granted Critical
Publication of US4526979A publication Critical patent/US4526979A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Definitions

  • the present invention relates to amide derivatives of amino-N-(1H-tetrazol-5-yl)benzamides. More particularly, it relates to aminobenzamides of the type referred to above wherein the amino group is substituted by an alkoxy carbonyl group or by an oxalyl ester group.
  • the present invention is directed to compounds having the following general formula: ##STR1## wherein n is 1 or 2; X is hydrogen or chlorine; and R is alkyl of 1-6 carbon atoms; and the pharmaceutically acceptable salts thereof.
  • the amine substituent can be in any isomeric position on the phenyl ring with respect to the carboxamide.
  • the amine group can be ortho, meta or para with respect to the carboxamide.
  • alkyl group referred to above are methyl, ethyl, propyl, butyl, isobutyl and hexyl with methyl and ethyl being preferred.
  • salts are the pharmaceutically acceptable salts and also the hydrates of the compounds and their salts.
  • pharmaceutically acceptable salts as used herein is intended to include non-toxic cationic salts such as the alkali metal salts, e.g., sodium and potassium; alkaline earth metal salts such as calcium, magnesium or barium; salts with ammonia; and salts with organic bases, e.g., amines such as triethylamine, n-propylamine and tri-n-butylamine.
  • the compounds of the present invention are prepared by the reaction of a 2-aminobenzamide of the formula: ##STR2## wherein X is defined as above, with an acid chloride of the formula: ##STR3## wherein n and R are defined as above.
  • the reaction is carried out in an inert solvent such as dimethylformamide.
  • an inert solvent such as dimethylformamide.
  • the reaction does take place without the application of external heat and, depending on the specific reactants, may in fact be exothermic, the mixture is generally heated to ensure completion of the reaction.
  • the product is isolated from the reaction mixture by standard procedures and, when dimethylformamide is used as the solvent, this consists of diluting the mixture with water and then cooling it.
  • the aminobenzamides shown above can be reacted with a strong base, such as sodium ethoxide, and an appropriate dicarboxylic acid alkyl ester, such as ethyl oxalate or ethyl carbonate.
  • a strong base such as sodium ethoxide
  • an appropriate dicarboxylic acid alkyl ester such as ethyl oxalate or ethyl carbonate.
  • the aminobenzamides used as the starting material in the above process are obtained by catalytic hydrogenation of a solution of the appropriate nitrobenzamide.
  • the preferred catalyst is 5% Pd/C although similar catalysts, such as Pt/C, can also be used.
  • the starting tetrazole can be dissolved in aqueous 1 N sodium hydroxide solution and, if necessary, this can be diluted with ethanol or additional water. Alternatively, the reduction can be carried out in acetic acid solution.
  • the necessary nitrobenzamide is obtained from the appropriate nitrobenzoyl chloride by reaction with 5-aminotetrazole and the necessary acid chloride is obtained from the corresponding carboxylic acid, with standard procedures used for both reactions.
  • the compounds obtained above are converted to the pharmaceutically acceptable salts by reacting the tetrazole final product with a substantially equimolar amount of the appropriate base in an aqueous solution or in a suitable organic solvent such as methanol or ethanol.
  • the salts are recovered by standard methods such as filtration if they are insoluble in the original medium, or, if they are soluble in that medium, the salt is precipitated by evaporation of the solvent or by addition of a non-solvent for the salt.
  • the compounds of the present invention possess antiallergic activity. Thus, they are useful in the treatment of conditions in which antigen-antibody reactions are responsible for disease and particularly in the treatment of allergic diseases such as (but not limited to) extrinsic asthma, hay fever, urticaria, eczema or atopic dermititis and upper respiratory conditions such as allergic rhinitis.
  • allergic diseases such as (but not limited to) extrinsic asthma, hay fever, urticaria, eczema or atopic dermititis and upper respiratory conditions such as allergic rhinitis.
  • the compounds of the present invention may be administered either as individual therapeutic agents or as mixtures with other therapeutic agents. They may be administered alone but are generally administered in the form of pharmaceutical compositions, i.e., mixtures of the active agents with suitable pharmaceutical carriers or diluents. Examples of such compositions include aerosol sprays, aqueous or oily suspensions and aqueous solutions for injection.
  • the present compounds can be used in the same general way as disodium cromoglycate
  • solutions or suspensions of a compound of the present invention with conventional pharmaceutical vehicles may be employed, e.g., as an aerosol spray for inhalation, as an aqueous solution for intravenous injection or an oily suspension for intramuscular injection.
  • the compounds may also be administered by means of inhalers or other devices which permit the active compounds in the form of dry powders to come into direct contact with the lungs.
  • the indicated compositions can be prepared by known techniques as described in standard texts such as Remington's Pharmaceutical Sciences, Mack Publishing Company, Easton, Pennsylvania.
  • the antiallergic activity of the present compounds is demonstrated by the IgE mediated rat Passive Cutaneous Anaphylaxis (PCA) test. This test is generally accepted as one of the best animal models for the qualitative determination of antiallergic activity. Disodium cromoglycate is active in this test when administered i.p. but not orally. The method can be described briefly as follows:
  • Sensitization--Recipient rats were passively sensitized by the intradermal injection of 100 microliters of two dilutions of antiserum (one injection on each side of the back). Sensitization ocurred 48-72 hours prior to antigen challenge.
  • Test Compound--Four administered to six animals for each test compound/dilution.
  • Compounds were homogenized in an appropriate carrier solution, and administered i.p. at 60 mg/kg 5 minutes prior to challenge.
  • a solution was prepared from 19 g of 2-nitro-N-(1H-tetrazol-5-yl)benzamide in 100 ml of aqueous 1 N sodium hydroxide and 100 ml of ethanol.
  • a 0.5-gram quantity of 5% Pd/C catalyst was added and the mixture was hydrogenated in a Parr apparatus at 1520 mm Hg pressure until uptake of hydrogen stopped.
  • the catalyst was removed by filtration and the filtrate was treated with aqueous 1 N hydrochloric acid.
  • the white solid which formed was separated by filtration and dried to give 2-amino-N-(1H-tetrazol-5-yl)benzamide melting at about 253°-254° C.
  • a slurry of 10 g of 3-nitro-N-(1H-tetrazol-5-yl)-benzamide and 250 ml of 70% acetic acid was treated with 1 g of 10% Pd/C and hydrogenated in a Parr apparatus at about 2550 mm Hg for 2.5 hours. The mixture was then filtered to separate the white solid and catalyst. The mixture of solids obtained was slurried with 250 ml of hot dimethylformamide and filtered. The resulting filtrate was diluted slowly with 250 ml of water and the resulting warm solution was filtered to remove a small amount of gelatinous material. The yellow crystalline solid which formed in the filtrate on cooling was separated by filtration and oven-dried to give 3-amino-N-(1H-tetrazol-1-yl)benzamide melting at about 281° C. with decomposition.
  • Example 7 The procedure of Example 7 was repeated using other amino-N-(1H-tetrazol-5-yl)benzamides and appropriate alkyl oxalyl chlorides. The reaction conditions used were generally similar to those described above. The following compounds were obtained:

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pulmonology (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US06/517,085 1983-07-22 1983-07-22 Carbamates and oxalamides of amino-N-(1H-tetrazol-5-yl)benzamides Expired - Lifetime US4526979A (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
US06/517,085 US4526979A (en) 1983-07-22 1983-07-22 Carbamates and oxalamides of amino-N-(1H-tetrazol-5-yl)benzamides
AU30222/84A AU561513B2 (en) 1983-07-22 1984-07-03 Carbamates and oxalamides of ammo-n-(1h-tetrazol-5-yl) benzamides
CA000459075A CA1220209A (en) 1983-07-22 1984-07-17 Carbamates and oxalamides of amino-n-(1h-tetrazol-5- yl)benzamides
JP59147033A JPS6042371A (ja) 1983-07-22 1984-07-17 アミノ−ｎ−（１ｈ−テトラゾ−ル−５−イル）ベンズアミド類のカルバメ−ト及びオキサラミド類
ZA845518A ZA845518B (en) 1983-07-22 1984-07-17 Carbamates and oxalamides of amino-n-(1h-tetrazol-5-yl)benzamides
AT84108508T ATE30024T1 (de) 1983-07-22 1984-07-18 Carbamate und oxalylamide von amino-n-(1htetrazol-5-yl)benzamiden.
IL72431A IL72431A (en) 1983-07-22 1984-07-18 Alkoxyalkylamino and alkoxycarbonyl amino n-(1h-tetrazol-5-yl)benzamides and their preparation
NZ208935A NZ208935A (en) 1983-07-22 1984-07-18 Carbamates and oxalamides of amino-n-(1h-tetrazol-5-yl)-benzamides
EP84108508A EP0135032B1 (en) 1983-07-22 1984-07-18 Carbamates and oxalyl amides of amino-n-(1h-tetrazol-5-yl) benzamides
DE8484108508T DE3466537D1 (en) 1983-07-22 1984-07-18 Carbamates and oxalyl amides of amino-n-(1h-tetrazol-5-yl) benzamides
PT78944A PT78944B (en) 1983-07-22 1984-07-19 Process for the preparation of carbamates and oxalamides of amino-n-(1h-tetrazol-5-yl)benzamides
GR75368A GR82102B (enrdf_load_stackoverflow) 1983-07-22 1984-07-19
HU842827A HU191431B (en) 1983-07-22 1984-07-20 Process for producing amino-n-/1h-tetrazol-5-yl/-benzamide derivatives
IE1894/84A IE57604B1 (en) 1983-07-22 1984-07-20 Carbamates and oxalyl amides of amino-n-(1h-tetrazol-5-yl)benzamides
ES534532A ES534532A0 (es) 1983-07-22 1984-07-20 Un procedimiento para preparar derivados de benzamida.
DK358584A DK159776C (da) 1983-07-22 1984-07-20 Carbamater og oxalamider af amino-n-(1h-tetrazol-5-yl)-benzamider og fremgangsmaade til fremstilling heraf
NO842967A NO168641C (no) 1983-07-22 1984-07-20 Analogifremgangsmaate ved fremstilling av terapeutisk aktive carbamater og oxalamider av amino-n-(1h-tetrazol-5-yl)benzamider.
KR1019840004338A KR890000534B1 (ko) 1983-07-22 1984-07-21 아미노-n-(1h-테트라졸-5-일)벤즈아미드의 카바메이트 및 옥살아미드 및 이의 제조방법

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/517,085 US4526979A (en) 1983-07-22 1983-07-22 Carbamates and oxalamides of amino-N-(1H-tetrazol-5-yl)benzamides

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US06/517,085 Expired - Lifetime US4526979A (en) 1983-07-22 1983-07-22 Carbamates and oxalamides of amino-N-(1H-tetrazol-5-yl)benzamides

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US (1) US4526979A (enrdf_load_stackoverflow)
EP (1) EP0135032B1 (enrdf_load_stackoverflow)
JP (1) JPS6042371A (enrdf_load_stackoverflow)
KR (1) KR890000534B1 (enrdf_load_stackoverflow)
AT (1) ATE30024T1 (enrdf_load_stackoverflow)
AU (1) AU561513B2 (enrdf_load_stackoverflow)
CA (1) CA1220209A (enrdf_load_stackoverflow)
DE (1) DE3466537D1 (enrdf_load_stackoverflow)
DK (1) DK159776C (enrdf_load_stackoverflow)
ES (1) ES534532A0 (enrdf_load_stackoverflow)
GR (1) GR82102B (enrdf_load_stackoverflow)
HU (1) HU191431B (enrdf_load_stackoverflow)
IE (1) IE57604B1 (enrdf_load_stackoverflow)
IL (1) IL72431A (enrdf_load_stackoverflow)
NO (1) NO168641C (enrdf_load_stackoverflow)
NZ (1) NZ208935A (enrdf_load_stackoverflow)
PT (1) PT78944B (enrdf_load_stackoverflow)
ZA (1) ZA845518B (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4879295A (en) * 1986-09-27 1989-11-07 Sawai Pharmaceutical Co., Ltd. N-tetrazolyl thiazolecarboxyamide derivatives and their use
US4946855A (en) * 1987-12-14 1990-08-07 Sawai Pharmaceutical Co., Ltd. Carboxamide derivatives having tetrazole and thiazole rings and their use
US20070027154A1 (en) * 2003-08-29 2007-02-01 Mitsui Chemicals., Inc. Insecticide for agricultural or horticultural use and method of use thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230148602A1 (en) * 2020-03-23 2023-05-18 Nippon Soda Co., Ltd. Benzamide compound and herbicide

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3824249A (en) * 1971-06-15 1974-07-16 Rech Medicale Soc D Acylamino tetrazoles
US4176631A (en) * 1975-05-27 1979-12-04 Mitsuhiro Kanao Internal combustion engine

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1561350A (en) * 1976-11-05 1980-02-20 May & Baker Ltd Benzamide derivatives
BE845612A (fr) * 1976-03-23 1977-02-28 Derives de tetrazole-5-carboxamide et leur preparation
GB1588242A (en) * 1977-10-28 1981-04-23 May & Baker Ltd N-(tetrazol-5-yl)-salicylamide derivatives
JPS5795984A (en) * 1980-12-05 1982-06-15 Tanabe Seiyaku Co Ltd Pyridinecarboxamide derivative and its preparation
DE3202065A1 (de) * 1982-01-23 1983-08-04 Basf Ag, 6700 Ludwigshafen Substituierte n-(tetrazol-5-yl)-benzoesaeureamide, ihre herstellung und diese enthaltende pharmazeutische zubereitungen

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3824249A (en) * 1971-06-15 1974-07-16 Rech Medicale Soc D Acylamino tetrazoles
US4176631A (en) * 1975-05-27 1979-12-04 Mitsuhiro Kanao Internal combustion engine

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Moffett et al., J. Med. Chem., 14(10), pp. 963 968 (1971). *
Moffett et al., J. Med. Chem., 14(10), pp. 963-968 (1971).

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4879295A (en) * 1986-09-27 1989-11-07 Sawai Pharmaceutical Co., Ltd. N-tetrazolyl thiazolecarboxyamide derivatives and their use
US4946855A (en) * 1987-12-14 1990-08-07 Sawai Pharmaceutical Co., Ltd. Carboxamide derivatives having tetrazole and thiazole rings and their use
US20070027154A1 (en) * 2003-08-29 2007-02-01 Mitsui Chemicals., Inc. Insecticide for agricultural or horticultural use and method of use thereof
AU2004268104B2 (en) * 2003-08-29 2009-01-08 Mitsui Chemicals, Inc. Insecticide for agricultural or horticultural use and method of use thereof
AU2004268104B9 (en) * 2003-08-29 2009-03-26 Mitsui Chemicals, Inc. Insecticide for agricultural or horticultural use and method of use thereof
US8158814B2 (en) 2003-08-29 2012-04-17 Mitsui Chemicals, Inc. Insecticide for agricultural or horticultural use and method of use thereof
US8816128B2 (en) 2003-08-29 2014-08-26 Mitsui Chemicals, Inc. Insecticide for agricultural or horticultural use and method of use thereof
US9089133B2 (en) 2003-08-29 2015-07-28 Mitsui Chemicals, Inc. Insecticide for agricultural or horticultural use and method of use thereof
US9101135B2 (en) 2003-08-29 2015-08-11 Mitsui Chemicals, Inc. Agricultural/horticultural insecticide and method for using the same

Also Published As

Publication number Publication date
HUT34461A (en) 1985-03-28
AU3022284A (en) 1985-01-24
NZ208935A (en) 1987-01-23
JPS6042371A (ja) 1985-03-06
NO842967L (no) 1985-01-23
KR850001181A (ko) 1985-03-16
ZA845518B (en) 1985-03-27
CA1220209A (en) 1987-04-07
NO168641C (no) 1992-03-18
GR82102B (enrdf_load_stackoverflow) 1984-12-13
KR890000534B1 (ko) 1989-03-20
AU561513B2 (en) 1987-05-07
NO168641B (no) 1991-12-09
IE841894L (en) 1985-01-22
HU191431B (en) 1987-02-27
DE3466537D1 (en) 1987-11-05
DK159776B (da) 1990-12-03
IE57604B1 (en) 1993-01-27
DK358584D0 (da) 1984-07-20
IL72431A (en) 1988-04-29
EP0135032B1 (en) 1987-09-30
ES8507518A1 (es) 1985-09-01
EP0135032A1 (en) 1985-03-27
ES534532A0 (es) 1985-09-01
ATE30024T1 (de) 1987-10-15
JPH0434994B2 (enrdf_load_stackoverflow) 1992-06-09
DK159776C (da) 1991-05-06
IL72431A0 (en) 1984-11-30
PT78944B (en) 1986-06-02
PT78944A (en) 1984-08-01
DK358584A (da) 1985-01-23

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